Triphenylphosphine → HCID 46836199, compound

HRID 474212Notes

Reaction equation

HRID 474212 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)=[N:13]2)=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:47]1(O)[CH2:51][CH2:50][CH:49]([OH:52])[CH2:48]1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C>[OH:52][CH:49]1[CH2:50][CH2:51][CH:47]([O:1][C:2]2[CH:3]=[N:4][C:5]([C:8]3[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=3)[CH2:11][N:12]3[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[N:13]3)=[N:6][CH:7]=2)[CH2:48]1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 97268Di-tert-butyl azodicarboxylate2×HCID 100165Cyclopentane-1,3-diolHCID 59438049HCID 59438049, compound

Product 1

HCID 46836199HCID 46836199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.28 mmol) of 2-[3-(5-hydroxypyrimidin-2-yl)benzyl]-6-(1-methyl-1H-pyrazol-4-yl)-2H-pyridazin-3-one are dissolved in 6 ml of DMF, and 277 mg (0.83 mmol) of polymer-bound triphenylphosphine (3 mmol/g) and 33 mg (0.32 mmol) of 1,3-cyclopentanediol are added. The reaction mixture is shaken at room temperature for 15 min, and 196 mg (0.83 mmol) of di-tert-butyl azodicarboxylate are subsequently added. The reaction mix-ture was shaken at room temperature for 3 h, a further 277 mg (0.83 mmol) of polymer-bound triphenylphosphine (3 mmol/g) and 196 mg (0.83 mmol) of di-tert-butyl azodicarboxylate were added, and the mixture was shaken at room temperature for 18 h. The reaction mixture is filtered off through kieselguhr with suction and washed with acetonitrile. The filtrate is evaporated and purified by means of preparative HPLC.

Workup

  1. additionThe reaction mix-ture
  2. stirringwas shaken at room temperature for 3 h
  3. stirringthe mixture was shaken at room temperature for 18 h
  4. filtrationThe reaction mixture is filtered off through kieselguhr with suction
  5. washwashed with acetonitrile
  6. customThe filtrate is evaporated
  7. custompurified by means of preparative HPLC

Sources & evidence

ORD record
ord-e9eb59344b0d42c0b317ad287184d618
Source dataset
uspto-grants-2014_01
Patent number
US08637518B2

Reaction notes

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